BRPI0614148A2 - compositions for use in agriculture comprising an oil-in-water emulsion based on oily globules coated with a liquid crystal lamellar coating - Google Patents

Abstract

COMPOSITIONS FOR USE IN AGRICULTURE UNDERSTANDING AN EMULSION OF OIL IN WATER BASED ON OIL BLOODS COATED WITH A LAMELLAR COATING OF LIQUID CRYSTAL. The present invention relates to a composition comprising an oil-in-water emulsion, in which the emulsion comprises oil globules provided individually with a liquid crystal lamellar coating and dispersed in an aqueous phase, in which each oil globule comprises at least one compound which is agriculturally active, individually coated with a monolamellar or oligolamellar layer comprising: (1) at least one non-ionic lipophilic active surface agent; (2) at least one non-ionic hydrophilic active surface agent; and (3) at least one ionic surface active agent; and also in which the oily globules have an average particle diameter of less than 800 nanometers.

Description

Patent Descriptive Report for "COMPOSITIONS FOR USE IN AGRICULTURE UNDERSTANDING A WATER-BASED OIL EMULSION COATED WITH A LIQUID CRYSTAL LAMEL COATING".

This patent application claims the benefits of United States Provisional Patent Applications No. 60 / 703,525, filed July 28, 2005 and No. 60 / 730,529 filed October 26, 2005.

The present invention relates to stable oil-in-water emulsion compounds for agricultural purposes.

Concentrated oil-in-water emulsions, active liquid ingredients or active ingredients dissolved in a solvent are commonly used in agricultural compositions due to certain advantages over other types of formulations. Emulsions are water-based preparations containing little or no solvents that allow mixtures of active ingredients to be combined into a single formulation and compatible with a wide variety of packaging materials. However, there are also several disadvantages to these agricultural emulsions. that is, they are often complex formulations that want large amounts of surface active agent for stabilization, are generally very viscous, have a tendency for Oswald emulsion globules to develop and separate over time. Therefore, improvements in these emulsion formulations are necessary in the agricultural field.

Various oil-in-water emulsion compositions for cosmetic and dermatological purposes have been described in U.S. Patent Nos. 5,658,575; 5,925,364; 5,753,241; 5,925,341; 6,066,328; 6,120,778; 6,126,948; 6,689,371; 6,419,946; 6,541,018; 6,335,022; 6,274,150; 6,375,960; 6,464,990; 6,413,527; 6,461,625 and 6,902,737. However, although these types of emulsions have advantageous use in personal care products, these types of emulsions have not been used previously with agricultural active compounds, which are typically present in emulsions at much higher levels than cosmetic ingredients. active.

The present invention relates to agricultural compositions comprising an oil-in-water emulsion, wherein the oil-in-water emulsion comprises oil globules dispersed in an aqueous phase, wherein the oil globules contain an agriculturally active compound, and are stable. with a liquid crystal lamellar coating.

One aspect of the present invention is a novel oil-in-water emulsion composition comprising:

A) an oil phase which comprises oily blood cells comprising at least one compound which is agriculturally active; and

B) an aqueous phase;

wherein the oily globules are dispersed in an aqueous phase and coated with a liquid crystal lamellar coating which comprises:

(1) at least one nonionic lipophilic surface active agent,

(2) at least one nonionic hydrophilic active surface agent and

(3) at least one ionic surface active agent, and where the oily globules have an average particle diameter of less than 800 nanometers.

The oil phase (A) of the oil-in-water emulsion of the present invention uses an agriculturally active compound, which is in the form of an oil, or alternatively, an agriculturally active compound, dissolved or mixed in an oil, to form the oily blood cells. By definition, an oil is a liquid that is not soluble in water. Any oil that is compatible with the agriculturally active compound may be used in the oil-in-water emulsions of the present invention. The term "compatible" means that the oil will dissolve or mix evenly with the a-crop-active compound and allow the formation of the oil-in-water emulsion oil globules of the present invention. Examples of oils include, but are not limited to, short chain fatty acid triglycerides, silicone oils, petroleum fractions or hydrocarbons such as heavy naphtha aromatic solvents, naphthalene aromatic solvents, petroleum distillates light hydrotreated, paraffinic, oleomineral solvents, alkylbenzenes, paraffinic oils, and the like; vegetable oils, such as, for example, soybean oil, rapeseed oil, decoco oil, cottonseed oil, palm oil, soybean oil, and the like; alkylated vegetable oils and fatty acid alkylesters such as for example methyl oleate and the like.

An agriculturally active compound is defined herein as any oil soluble oily compound or hydrophobic compound having any pesticidal or biocidal activity; it being understood to refer to the active compound itself when it is an oil or alternatively the active compound is dissolved in an oil. Thus, such compounds or pesticides include fungicides, insecticides, nematocides, miticides, cupimicides, termiticides, rodenticides, arthropodicides, herbicides, biocides and the like.

Examples of these agriculturally active ingredients can be found in the "Pesticide Handbook, 12th edition". Examples of pesticides which may be used in the oil-in-water emulsion of the present invention include, but are not limited to, benzofuranyl methylcarbamate insecticides such as benfuracarb, and carbosulfan; oxime carbamate insecticides, such as aldicarb; fumigation insecticides, such as chloropicrin, 1,3-dichloropropene and methyl bromide; juvenile hormone mimicking agents, such as phenoxycarb; organophosphate-based insecticides, such as dichlorostics; aliphatic organothiophosphate-based insecticides such as, for example, malation and terbufos; aliphatic amide-based organothiophosphate insecticides such as dimethoate; benzotriazine organothiophosphate insecticides, such as azinphos-ethyl and azinphos-methyl; pyridine organothio phosphate insecticides, such as chloropyrifos and chloropyrifos-methyl; depyrimidine organothiophosphate insecticides such as diazinon; phenylorganothiophosphate insecticides, such as paration and paration methyl; pyrethroid ester insecticides, such as, for example, bifentrin, cyflutrin, beta-cyflutrin, cyhalothrin, gamma-cyialotrin, lamda-cyialotrin, cypermethrin, alpha-cypermetrin, beta-cypermethrin, fenvalerate, and permetrin; and the like.

Examples of herbicides which may be used in the oil-in-water emulsion of the present invention include, but are not limited to: amide-derived herbicides such as dimethenamid and dimethanamide-P; anilide herbicides, such as propanyl; decoroacetanilide herbicides, such as, for example, acetochlor, alachlor, butachlor, metolachlor and S-metolachlor; cyclohexene oxime herbicides, for example, methoxydim; dinitroaniline herbicides, such as, for example, benfluralin, etalfluralin, pendimethalin, and trifluralin; nitrile herbicides such as bromoxynil octanoate; phenoxyacetic herbicides such as 4-CPA, 2,4-D, 3,4-DA, MCPA, and MCPA-thioethyl; phenoxybutyric herbicides, such as, for example, 4-CPB, 2,4-DB, 3,4-DB, and MCPB; phenoxypropionic herbicides, such as, for example, cloprop, 4-CPP, dichloroprop, dichloro-prop-P, 3,4-DP, fenoprop, mecoprop and mecoprop-P; aryloxife-noxypropionic herbicides, such as, for example, cialofop, fluazifop, fluazifop-P, haloxifop, haloxifop-R; pyridine herbicides, such as, for example, aminopyralid, chlopyridid, fluroxipyr, pichloram, and triclopyr; triazole herbicides such as ethyl carfentrazone; and the like.

Herbicides may also generally be employed in combination with known safety herbicides, such as benoxacor, cloquintocet, ciometrinyl, daimuron, dichloromid, dicyclonon, diethylate, fenclorazole, fenclorazol-ethyl, fenclorim, flurazol, fluxophenim, furilazol, , isoxadifen-ethyl, mefenpir, mefenpir-diethyl, MG191, MON4660, R29148, mefenate, naphthalic anhydride, N-phenylsulfonylbenzoic acid amides and oxabetrinyl.

Examples of fungicides which may be used in the oil-in-water emulsion of the present invention include, but are not limited to, diphenoconazole, dimethomorph, dinocap, diphenylamine, dodemorf, edifenphos, fenemolol, fenbuconazole, fenpropimorph, miclobutanil, oleic acid (acids). propiconazole, tebuconazole and the like. Those skilled in the art understand that any agriculturally decomposed combination can also be used in the oil-in-water emulsion of the present invention, provided that a stable and effective emulsion is obtained.

The amount of agriculturally active ingredient in the oil-in-water emulsion will vary depending upon the effective active ingredient, the application of the agriculturally active ingredient and the appropriate levels of application which are well known to those skilled in the art. Typically, the total amount of the agriculturally active ingredient in the oil-in-water emulsion will be 1, generally 5, preferably 10, most preferably 15 and most preferably 20 to 45; It is generally 40, preferably 35 and most preferably 30% by weight, based on the total weight of the oil-in-water emulsion.

The liquid crystal lamellar coating is an extremely thin mono- or oligolamellar layer. The oligolamellar layer is understood to refer to a layer comprising from 2 to 5 lipid lines. Liquid crystal lamellar coating can be detected by Transmission Electron Microscopy after cryofracture or negative staining, X-ray diffraction or Optical Microscopy under polarized light. The terms and structure of the Iamelar crystal liquid phase are well defined in the publication "The Colloidal Domain", second edition, by D. FennellEvans and H. Wennerstrom, WiIey-VCH (1999), pages 295-296 and 306-307. The oligolamellar layer comprises surface active agents (1), (2) and (3) as indicated above. Preferably, the lipophilic active surface agent (1), and the hydrophilic active surface agent (2) individually contain at least one of the optionally saturated and / or branched fatty hydrocarbon chain having more than 12 carbon atoms, preferably from 16 to 22 carbon atoms.

Preferably, the lipophilic surface active agent (1) has an HLB between 2 and 5. HLB is a standard term known to those skilled in the art and refers to the Lipophilic Hydrophilic Balance, which identifies the solubility of the emulsifier in water or oil. The term lipophilic is understood as the ability of a material to dissolve in a fat or lipid type solvent. The lipophilic active surface agent is typically selected from optionally ethoxylated mono- or polyalkyl ethers, glycerol or polyglycerol esters, mono- or polyalkyl esters or (optionally ethoxylated) sorbitan esters, mono- or polyalkyl ethers. or pentaerythritol esters, mono- or polyalkyl ethers or polyoxyethylene esters, and mono- or polyalkyl ethers of sugar esters. Examples of lipophilic surface active agent (1) include, but are not limited to, sucrose distearate, diglyceryl distearate, tetraglyceryl distearate, decaglyceride decestearate, diglyceryl monostearate, hexaglyceryl distearate, pentaestearate, sorbitan monostearate, sorbitan stearate, diethylene glycol monostearate, glycerol ester and palmitic and stearic acids, polyoxyethylenated 2 EO monostearate (containing 2 units of ethylene oxide), glyceryl mono- and dibeenate and pentaerythrate tetraestearate.

The term hydrophilic is understood as the affinity of a material to be associated with water. The hydrophilic surface active agent typically has an HLB of 8 to 12 and are typically selected from the group consisting of polyethoxylated sorbite mono- or polyalkyl ethers, polyoxyethylene mono- or polyalkyl ethers, esters or esters polyglycerol mono- or polyalkyls, polyoxyethylene block copolymers with polyoxypropylene or polyoxybutylene and optionally ethoxylated sugar mono- or polyalkyl esters or esters. Examples of hydrophilic active surface agents (2) include, but are not limited to, polyoxyethylenated 4 EO sorbitan monostearate, 20 EO polyoxyethylene sorbitan stearate, 20 EO polyoxyethylene sorbitan stearate, 8 EO polyoxyethylenated monostearate, hexa-glyceryl monostearate, polyoxyethylenated 10 EO monostearate, polyoxyethylenated 12 EO distearate and polyoxyethylenated methyl glycoside distearate 20 EO.

In addition to the lipophilic and hydrophilic surface active agents, the ionic surface active agent (3) also comprises the oligola-melar layer of the liquid crystal lamellar coating. The surface active tonic agents that can be used in the oil-in-water emulsion of the present invention. include: (a) neutralized anionic surface active agents, (b) amphoteric surface active agents, (c) alkylsulfonic derivatives and (d) cationic surface active agents.

Neutralized anionic active surface agents (a) include, without limitation, for example:

alkali metal salts of dicetyl phosphate and dimyristyl phosphate, in particular sodium and potassium salts;

- alkali metal salts of cholesteryl sulfate and cholesteryl phosphate, especially sodium salts;

- lipoamino acids and their salts, such as, for example, monosodium and disodium acylglutamates, such as, for example, the disodium salt of N-stearoyl-L-glutamic acid, the sodium salts of phosphatidic acid;

- phospholipids; and

- monosodium and disodium salts of acylglutamic acids, in particular N-stearoylglutamic acid.

Anionic surface active agents selected from the group consisting of alkyl ether citrates and mixtures thereof which may be used in the oil-in-water emulsion of the present invention are described in United States Patent 6,413,527. monoesters or diesters formed by citric acid and at least one oxyethylene fatty alcohol comprising a straight or branched saturated or unsaturated alkyl chain comprising from 8 to 22 carbon atoms and comprising from 3 to 9 oxyethylene groups and mixtures thereof. These citrates may be selected, for example, from the group consisting of monoesters and diesters of citric acid and ethoxylated lauryl alcohol comprising from 3 to 9 oxyethylene groups. Alkyl ether citrates are preferably employed in neutral form at pH 7. Neutralizing agents may be selected from inorganic bases such as sodium hydroxide, potassium hydroxide or ammonia and organic bases such as mono, di- and triethanolamine, aminomethyl. -1,3-propanediol, N-methylglycine, basic amino acids such as arginine and lysine, and mixtures thereof.

Amphoteric active surface agents (b) include, but are not limited to, phospholipids and especially pure soybean phosphatidylethanolamine.

Alkylsulfonic derivatives (c) include, but are not limited to, the compounds of Formula:

<formula> formula see original document page 9 </formula>

wherein R represents CieH33 and CieH37 radicals, considered as a mixture or separately, and M is an alkali metal, preferably sodium.

Cationic surface active agents (d) include, but are not limited to, surface active agents as described in U.S. Patent No. 6,464,990. These are typically selected from the group consisting of quaternary ammonium salts, fatty amines and salts thereof.

Quaternary ammonium salts include, for example, those having the following formula:

<formula> formula see original document page 9 </formula>

wherein the radicals R1 to R4, which may be identical or different, represent a linear or branched aliphatic radical, comprising from 1 to 30 carbon atoms or an aromatic radical such as aryl or alkylaryl. Aliphatic radicals may comprise heteroatoms such as oxygen, nitrogen, sulfur and halogens. Aliphatic radicals include alkyl, alkoxy, (C2 -C6) polyoxyalkylene, alkylamido, (C12 -C22) alkyl starch, (C2 -C22) alkyl acetate and hydroxyalkyl radicals comprising approximately 1 at 30 carbon atoms; X is an anion selected from the group consisting of (C2 -C6) alkyl halides, phosphates, acetates, lactates, sulfates, and alkyl or alkylaryl sulfonates. Preference is given to quaternary ammonium salts rather than tetralkylammonium chloride such as dialkyl dimethyl ammonium and alkyl kiltrimethyl ammonium chlorides, in which the alkyl radical comprises approximately 12 to 22 carbon atoms, in particular chlorides. beenyltrimethyl ammonium, distearyldimethyl ammonium, cetyltrimethyl ammonium and benzyldimethylstearyl ammonium, or alternatively stearamidopropyl dimethyl chloride (demyristyl acetate) ammonium; quaternary amidazolinium ammonium salts, such as, for example, those of formula:

<formula> formula see original document page 10 </formula>

wherein R5 represents an alkenyl or alkyl radical, comprising from 8 carbon atoms, for example, derived from tallow fatty acids; R 6 represents a hydrogen atom, an alkyl radical comprising from 1 to 4 carbon atoms or an alkenyl or alkyl radical comprising from 8 to 30 carbon atoms; R7 represents an alkyl radical comprising 1 to 4 carbon atoms; R8 represents a hydrogen or alkyl radical comprising from 1 to 4 carbon atoms; and X is an anion selected from the group of halides, phosphates, acetates, lactates, alkyl sulfates or alkyl and alkylaryl sulfonates. R5 and R6 preferably have a mixture of alkenyl or alkyl radicals comprising from 12 to 21 carbon atoms, for example derived from tallow fatty acids, R7 preferably has a methyl radical and R8 has It preferably contains hydrogen. Quaternary diammonium salts are also contemplated, such as propane-tallow diammonium dichloride.

Fatty amines include, but are not limited to, those of the formula:

R 9 (CONH) n (CH 2) m N (R 11) R 10

wherein R 9 is optionally a saturated and / or branched hydrocarbon chain having from 8 to 30 carbon atoms, preferably from 10 to 24 carbon atoms; R10 and R11 are selected from H and an optionally saturated and / or branched hydrocarbon chain having from 1 to 10 carbon atoms; preferably between 1 and 4 carbon atoms;

m is an integer between 1 and 10, preferably between 1 and 5; and η is 0 or 1.

Examples of fatty amines include, but are not limited to, stearylamine, aminoethyl ethanolamide stearate, diethylene triamine stearate, palmitamidopropyl dimethyl amine, palmitamidopropyldiethylamine, palmitamidemethylethylamine, palmitamidoethyldimethylamine. Commercially available fatty amines include, but are not limited to, Croda Incromina®BB, Nikkol Amidoamine® MSP, and Ino-lex Lexamine® Series, Kao Corp Acetamine Series; Berol 380, 390, 453 and 455, and Akzo Nobel's Ethomeen® series, and Marlazin® L10, OL2, 020, T15 / 2, T50 from Condea Chemie.

The active surface agents of (1), (2) and (3) form the liquid crystal lamellar coating of the oil globules suspended in the phase of the oil-in-water emulsion of the present invention. The amount of the three surface active agents, (1), (2) and (3), used in the oil-in-water emulsion of the present invention is typically 20, preferably 35 to 65, preferably 55% by weight of (1). 15, preferably 25 to 50, preferably 40 wt.% (2) and 5, preferably 10 to 45, preferably 35 wt.% (3); based on the combined total weight of (1), (2) and (3). The coating of the oil globules comprises a total amount of hydrophilic surface active agent, lipophilic surface active agent and surface active agent between 2 and 20% by weight, based on the total weight of the oil-in-water emulsion. Preferably the total amount is 2.5, more preferably 3 to 10, more preferably 6% by weight, based on the total weight of the oil-in-water emulsion.

The ratio of total weight of active surface compounds (1), (2) and (3) to total oil weight is typically 1: 2.5 to 1:25.

The aqueous phase (B) is typically water, for example deionized water. The aqueous phase may also contain other additives such as freezing point-lowering compounds such as alcohols, for example isopropyl alcohol and propylene glycol; pH buffering agents, for example alkaline phosphates such as monohydrate mono-basic sodium phosphate, dibasic sodium phosphate; biocides, for example Pro-xel GXL; and defoamers, for example octamethylcyclotetrasiloxane (Anti-foam A from Dow Corning). Other additives and / or adjuvants may also be present in an aqueous phase (B) provided that the stability of the oil-in-water emulsion is still maintained. Other additives also include agriculturally water-soluble active compounds.

The oil phase or coated oil globules are 5, preferably 8 and more preferably 10 to 50%, preferably 45, more preferably 40% by weight, based on the total weight of the oil emulsion in water composition. The oil / water ratio is typically less than or equal to 1.

Other additives and / or adjuvants may also be present in the oil-in-water emulsion of the present invention, provided that the stability and activity of the oil-in-water emulsion is still obtained. The oil-in-water emulsion of the present invention may additionally contain an active surface adjuvant to enhance the deposition, wetting and penetration of the agriculturally active ingredient at the target site, e.g., crop, weed or organism. These surface-active adjuvants may optionally be employed as an emulsion component in Phase A or B, or as a tanking component; the use of the desired amount being well known to those skilled in the art. Suitable surface active adjuvants include, but are not limited to, ethoxylated nonyl phenols, synthetic or natural ethoxylated alcohols, salts of esters or sulfosuccinic acids, ethoxylated or ganosilicones, ethoxylated fatty amines, and mixtures of surface active agent with mineral or vegetable oils.

The oil-in-water emulsion of the present invention may be prepared according to the process described in U.S. Patent No. 5,925,364. The mixture is homogenized by cavitation using a high pressure homogenizer to provide the smallest particle size oil globules. The average size of the coated oil globules is typically less than 800 nanometers, preferably less than 500 nanometers, and more preferably less than 200 nanometers, more preferably less than 150 nm, as determined using particle size analysis by. laser diffraction and electron scanning microscopy.

In one embodiment, the oil-in-water emulsion is prepared by means of:

1) mixing (A) an oil phase comprising the lipophilic surfactant, hydrophilic surfactant, tonic surfactant, an agriculturally active compound and optionally an oil and (B) an aqueous phase to obtain a mixture; and

2) homogenize the mixture by subjecting the mixture to cavitation.

In the first step, the mixture may be formed by conventional stirring, for example using a high shear homogenizer, rotating at a rate of about 2000 to 7000rpm, for a time of about 5 to 60 minutes and a temperature between about 20 ° C and 95 ° C.

Homogenization can be performed using a high pressure homogenizer operating at pressures between approximately 20MPa and 100 MPa (200 and 1000 bar), as "is well known to those skilled in the art. The process is performed by passages. successively, usually from 2 to 10 passes, at a selected pressure, mixing back to the normal pressure between each pass.The homogenization of the second step can also be performed under ultrasound or alternatively by the use of a homogenizer equipped with a head-type rotor-stator.

Another embodiment of the present invention is the use of the oil-in-water emulsion in agricultural applications to control, prevent or eliminate unwanted living organisms, for example, fungi, weeds, insects, bacteria or other microorganisms and other pests. This would include its use in protecting a plant against attack by a phytopathogenic organism or treating a plant already infested by a phytopathogenic organism, comprising applying an oil-in-water emulsion composition to the soil to a plant, a plant part, foliage, flowers, fruits, and / or seeds, for disease inhibition and in a phytologically acceptable amount. The term "disease inhibition and phytologically acceptable amount" refers to an amount of a compound that kills or inhibits plant disease, the control of which is desired, but not significantly toxic to the plant. The exact concentration required of an active compound varies with the fungal disease to be controlled, the type of formulations employed, the method of application, the specific plant species, climatic conditions, and the like, as is well known in the art.

Additionally, oil-in-water emulsions of the present invention are useful for controlling insects or other pests, for example rodents. Accordingly, the present invention is also directed to a method for inhibiting an insect or pest, the method of which comprises applying an insect or pest locally to an oil emulsion in water, comprising an amount of an agriculturally active insect inhibitor compound therefor. use. The "place" of insects or pests is a term here used to refer to the environment in which the insects or pests lived where their eggs are present, including the air around them, whatever they eat, or objects. that they touch. For example, insects that eat or touch edible or ornamental plants can be controlled by applying the active compound to parts of plants such as seed, shrub or seedling that is planted; leaves, stems, fruits, grains, or roots, or the soil on which the roots are growing. It is contemplated that agriculturally active compounds and oil-in-water emulsions containing them may also be useful for protecting fabrics, paper, stored grain, seeds, domesticated animals, buildings or humans by applying a compound. active in or near objects. The term "inhibiting an insect or pest" refers to a decrease in the number of living insects or pests, or a decrease in the number of viable insect eggs. The extent of the reduction accomplished by a compound certainly depends on the rate of application of the compound, the specific compound used, and the target insect or pest species. At least an inactivating amount should be used. The terms "insect or pest inactivating amount" are used to describe the amount that is sufficient to cause a measurable reduction in the treated insect or pest population, as is well known in the art.

The place to which a compound or composition is applied may be any place inhabited by an insect, mite or pest, for example vegetable, fruit and walnut crops, vines, ornamental plants, animal animals, the internal or external surfaces of buildings and the ground around buildings.

Because of the unique ability of insect eggs to withstand toxic action, repeated applications to control newly emerging larvae may be desirable, as is true of other known insecticides and acaricides.

Additionally, the present invention relates to the use of oil-in-water emulsions comprising agriculturally active compounds which are herbicidal. The term herbicide is used herein to mean an active ingredient that kills, controls or otherwise adversely modifies plant growth. An effective amount of herbicide or vegetation control is an amount of active ingredient that causes an adversely modifying effect and includes deviations from natural development, killing, regulation, dissection, retardation, and the like. The termsplants and vegetation include emerging seedlings and established vegetation.

Herbicidal activity is exhibited when applied directly to the unwanted plant site itself, at any stage of growth, before weeds appear. The effect observed depends on the plant species to be controlled, the growth stage of the plant, the particle size of the solid components, the environmental conditions at the time of use, the specific adjuvants and vehicles employed, the soil type, and the like, as well as amount of chemical applied. These and other factors may be adjusted as known in the art to promote selective herbicidal action. Generally, it is preferable to apply such herbicides after the emergence of relatively immature undesirable vegetation to achieve the maximum weed control.

Another specific aspect of the present invention is a method for preventing or controlling pests such as nematodes, mites, arthropods, rodents, termites, bacteria or other microorganisms, the method of which comprises applying a composition of the present invention to a location where the control or Prevention is desired, comprising the appropriate compound, such as, for example, a nematocide, miticide, arthropodicide, rodenticide, termiticide or biocide.

The effective amount of the agriculturally active compound to be applied at the site of disease, insects and mites, weeds or other pests is well known in the art and can readily be determined by those skilled in the art in view of the teachings. above.

The composition of the present invention surprisingly offers agriculturally stable oil-in-water emulsions having low viscosity and long shelf life. In addition, the agriculturally stable oil-in-water emulsions of the present invention may offer other surprising improvements such as, for example, enhanced efficiency.

The following examples are provided to illustrate the present invention. The examples are not intended to limit the scope of the present invention and should not be construed as such. Quantities are in parts by weight or by weight, except where otherwise indicated.

Examples

These examples are provided to further illustrate the invention and should not be construed as limiting the invention.

As described herein, all temperatures are given in degrees Celsius and all percentages are percent by weight unless otherwise indicated.

In these examples, the process is performed using the following procedure: The oil phase A and the aqueous phase B are separately heated to the desired temperature. Phase B is poured into phase A with agitation of 4000 - 8000 rpm provided by a Silverson L4RT shear homogenizer, fitted with a high shear square hole. Stirring conditions and temperature are maintained for 10 minutes.

The mixture is then introduced into a Panda 2K Niro Soa-vi 2-stage high-pressure homogenizer which is adjusted to a pressure of 50 MPa (500 bar) for 2 to 10 successive passes.

A stabilized emulsion of oil in water is then obtained, whose oily globules have an average diameter typically less than 200 nm.

Example 1: Oil-in-Water Emulsion - Methyl Haloxifop-R

<table> table see original document page 17 </column> </row> <table>

The two process steps were carried out at a temperature of 70 ° C. The size of the oil globules in the oil-in-water emulsion, as determined by a Malvern Zetasizer Device, was 154 nm. The oil-in-water emulsion was stable under 2-week accelerated storage test conditions. temperature of 54 ° C, no change in oily blood cell size and no sedimentation or sedimentation.Example 2: Oil-in-water emulsion - Methyl Haloxifop-R

<table> table see original document page 18 </column> </row> <table>

The two process steps were carried out at a temperature of 70 ° C. The size of the oil globules in the oil-in-water emulsion, as determined by a Malvern Mastersizer Device, was 184 nm.

Example 3: Oil-in-Water Emulsion - 2,4-D Butoxyethyl Ester

<table> table see original document page 18 </column> </row> <table>

The two process steps were carried out at a temperature of 70 ° C. The size of the oil globules in the oil-in-water emulsion, as determined by a Malvern Mastersizer Device, was 207nm. The oil-in-water emulsion was stable under accelerated 2-week accelerated storage test conditions at 54 ° C, with no change in oily cell size and no sedimentation.Example 4: Oil-in-emulsion Water - Cialofop Butyl Ester

<table> table see original document page 19 </column> </row> <table>

The two process steps were carried out at a temperature of 70 ° C. The size of the oil globules in the oil-in-water emulsion, as determined by a Malvem Mastersizer Device, was 197 nm. Oil-in-water emulsion was stable under 2-week accelerated storage test conditions at 54 ° C, with no change in oily cell size and no sedimentation or syneresis.

Example 5: Oil-in-Water Emulsion - Dinocap

<table> table see original document page 19 </column> </row> <table>

The two process steps were carried out at a temperature of 70 ° C. The size of the oil globules in the oil-in-water emulsion, as determined by a Malvern Mastersizer Device, was 213 nm. Oil-in-water emulsion was stable under 2-week accelerated storage test conditions at 54 ° C with no change in oily cell size and no sedimentation or syneresis.Example 6: Chlorpirifos Oil-in-Water Emulsion

<table> table see original document page 20 </column> </row> <table>

The two process steps were carried out at a temperature of 70 ° C. The size of the oil globules in the oil-in-water emulsion as determined by a Malvern Mastersizer Device was 180 nm. Oil-in-water emulsion was stable under 2-week accelerated storage test conditions at 54 ° C, with no change in oily cell size and no sedimentation or syneresis.

Example 7: Oil-in-Water Emulsion - Methylptil Fluroxipir Ester and Bu Toxyl Ethyl Triclopir

<table> table see original document page 20 </column> </row> <table>

Diglycerol Monostearate (Nikkol DGMS from Nikko Chemical Co.) 2,0 Sorbitan Stearate (40EO) (Uniqema Tween 61) 1,4

N-Stearoyl Disodium Glutamic Acid Salt (Aji-nomoto Amisoft HS-2IP)

<table> table see original document page 20 </column> </row> <table> The two process steps were performed at a temperature of 70 ° C. The size of the oil globules in the oil-in-water emulsion as determined by a Malvem Mastersizer Device was 186nm. The oil-in-water emulsion was stable under accelerated 2 week accelerated storage test conditions at 54 ° C, with no change in the size of the oily cells and no sedimentation or sedimentation.

Example 8: Oil-in-Water Emulsion - Cialofop Butyl Ester, Common Stabilized Cationic Surfactant

<table> table see original document page 21 </column> </row> <table>

The two process steps were carried out at a temperature of 70 ° C. The size of oily globules in the oil-in-water emulsion as determined by a Malvern Mastersizer Device was 196nm. The oil-in-water emulsion was stable at room temperature for two years, with no change in the size of the oily cells, no sedimentation or syneresis.Example 9: Oil-in-water emulsion with different Anionic Surfactants

<table> table see original document page 22 </column> </row> <table>

The two process steps were performed at 40 ° C. The overall composition of the oil-in-water emulsion is 30% oleomineral, 2.0% PEG-2 stearyl ether (marketed under the name Brij72 by Uniqema) 1.5% sorbitan stearate (40EO) (marketed under Tween 61 by Uniqema) and 0.5% anionic surfactant, as shown in the table above, with the balance being water.

The size of oily globules (D 0.5 nm) in the oil-in-water emulsion as determined by a Malvem Mastersizer Device was between 181 and 192 nm. The oil-in-water emulsions were stable under 1 week cycle storage test conditions at -10 ° C to 40 ° C, with no change in the size of the oil globules and no sedimentation or syneresis.

Surprisingly, it has also been found that the emulsions of the present invention have also been stable when using oils having an average molecular weight (MW) of less than 500, where prior art emulsions have typically used oils having a higher MW.

Claims (32)

An oil-in-water emulsion composition, comprising: a) an oil phase comprising oil globules comprising at least one compound which is agriculturally active; and b) an aqueous phase, wherein the oily globules are dispersed in the aqueous phase and are coated with a liquid crystal lamellar coating comprising: -1) at least one nonionic lipophilic active surface agent; nonionic hydrophilic active surface; and -3) at least one ionic surface active agent, and further wherein the oily globules have an average particle diameter of less than 800 nanometers. The composition of claim 1, wherein the nonionic lipophilic active surface agent has a Lipophilic Hydrophilic Balance between 2 and 5. A composition according to claim 2, wherein the nonionic lipophilic active surface agent is selected from the group consisting of optionally ethoxylated mono- or polyalkyl ethers or glycerol or polyglycerol esters, mono- or polyalkyl ethers or optionally ethoxylated desorbitan esters, mono- or polyalkyl ethers or pentaerythritol esters, mono- or polyalkyl ethers or polyoxyethylene esters and mono- or polyalkyl ethers or sugar esters. The composition of claim 3, wherein the nonionic lipophilic active surface is selected from the group consisting of sucrose distearate, diglyceryl distearate, tetraglyceryl distearate, decaglyceryl decearearate, diglyceryl monostearate, tristearate hexaglyceryl, decaglyceryl pentastearate, sorbitan monostearate, sorbitan triestearate, diethylene glycol monostearate, glycerol ester and palmitic and stearic acids, polyoxyethylenated 2 EO monostearate (containing 2 units of ethylene oxide) pentaerythritol tetraestearate. A composition according to claim 1, wherein the nonionic hydrophilic active surface agent has a Lipophilic Hydrophilic Balance between 8 and 12. A composition according to claim 5, wherein the nonionic hydrophilic active surface agent is selected from the group consisting of mono- or polyalkyl ethers or polyethoxylated sorbitan esters, mono- or polyalkyl ethers or esters. polyoxyethylene and mono- or polyalkyl ethers or polyglycerol esters, polyoxypropylene or polyoxybutylene block copolymers and optionally ethoxylated mono- or polyalkyl ethers or sugar esters. The composition according to claim 6, wherein the nonionic hydrophilic active surface agent is selected from the group consisting of polyoxyethylenated sorbitan monostearate 4 EO, polyoxyethylenated sorbitane stearate 20 EO, monostearate. polyoxyethylenated 8 EO, hexaglyceryl monostearate, polyoxyethylenated 10 EO monostearate, polyoxyethylenated 12 EO distearate and polyoxyethylenated methyl glycoside distearate 20 EO. The composition of claim 1, wherein the ionic active surface agent is selected from the group consisting of (a) neutralized anionic active surface agents; (b) amphoteric surface active agents; (c) alkylsulfonic derivatives; and (d) cationic surface active agents. The composition of claim 8, wherein the ionic surface active agent is selected from the group consisting of: • alkali metal salts of dicetyl phosphate and dimirisyl phosphate, in particular salts of sodium and potassium • alkali metal salts of cholesteryl sulfate and cholesteryl phosphate, especially sodium salts • lipoamino acids and their salts such as monosodium and disodium acylglutamates, such as salt N-stearoyl-L-glutamic acid disodium, the sodium salts of phosphatidic acid • phospholipids • monosodium and disodium salts of acylglutamic acids, in particular of N-stearoylglutamic acid; and • alkyl ether citrates. The composition of claim 8, wherein the ionic surface active agent is a phospholipid. A composition according to claim 8, wherein the ionic active surface agent is an alkylsulfonic derivative. A composition according to claim 8, wherein the ionic active surface is selected from the group consisting of quaternary ammonium salts, fatty amines and salts thereof. A composition according to claim 1 comprising: from 20 to 65 wt% of (1), 15 to 50 wt% of (2) and 5 to 45 wt% of (3), based on the total weights of (1), (2) and (3). The composition according to claim 1, wherein the agriculturally active compound is selected from the group consisting of fungicides, insecticides, nematocides, miticides, biocides, termiticides, rodenticides, arthropodicides and herbicides. The composition of claim 14, wherein the agriculturally active compound is a fungicide. A method of controlling or preventing a fungal attack comprising applying a composition as defined in claim 15 to the specific fungus, soil, plant, root, foliage, seed or place at which the infestation is to be prevented. or controlled. The composition according to claim 1, wherein the agriculturally active compound is an insecticide. Insect inhibition method, comprising applying to a location where control or prevention is desired, of a composition as defined in claim 17. The composition of claim 1, wherein the agriculturally active compound is a herbicide. A method of preventing or controlling unwanted vegetation, comprising applying to a location where control or prevention is desired, of a composition as defined in claim 19. The composition according to claim 1, wherein the agriculturally active compound is a nematocide. A method of preventing or controlling nematodes, comprising applying to a location where control or prevention is desired, of a composition as defined in claim 21. The composition of claim 1, wherein the agriculturally active compound is a miticide. A method of preventing or controlling mites, comprising applying to a location where control or prevention is desired, of a composition as defined in claim 23. The composition according to claim 1, wherein the agriculturally active compound is an anthropodicide. A method of preventing or controlling arthropods, comprising applying to a location where control or prevention is desired, of a composition as defined in claim 25. The composition according to claim 1, wherein the agriculturally active compound is a biocide. A method for the prevention or control of bacteria and other microorganisms, comprising applying to a location in which the prevention or control thereof is desired, of a composition as defined in claim 27. The composition according to claim 1, wherein the agriculturally active compound is a rodenticide. A method of rodent prevention or control, comprising applying to a location where control or prevention is desired, of a composition as defined in claim 29. The composition of claim 1, wherein the agriculturally active compound is a termiticide. A termite prevention or control method, comprising applying to a location where control or prevention is desired, of a composition as defined in claim 31.